There is something called Special enrollment period.
New borns, Job change, new job, kids returning home from college, people getting married, divorced, Prime hold deceased, etc are some of the exemptions when that will kick in.
If he changes job with employer providing option, he can get health insurance. Otherwise, hospitals will be happy to work with you if you tell them that you dont have insurance.
Dan, you should get the lowest HMO plan at least to have coverage after 40. This damn country never appreciate alternative medicines.